SENKIRKIN Chemical Properties

Melting point:

197°C

Boiling point:

497.19°C (rough estimate)

Density 

1.2439 (rough estimate)

refractive index 

1.5180 (estimate)

storage temp. 

-20°C

form 

Solid

pka

12.67±0.40(Predicted)

color 

White to off-white

LogP

0.690 (est)

IARC

3 (Vol. 31, Sup 7) 1987

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

RIDADR 

1544

WGK Germany 

3

HazardClass 

6.1(b)

PackingGroup 

III

Hazardous Substances Data

2318-18-5(Hazardous Substances Data)

SENKIRKIN Usage And Synthesis

Description

A further hepatotoxiC alkaloid present in Senecio kirkii Hook, S. renardi and Nardosrnia laevigata. The base has [α]²⁵_D - 16° (c 1.89, MeOH) or[α]¹⁵_D - 6.2° (c 1.91, CHCI₃). It forms colourless plates when crystallized from either Me₂CO or AcOEt and yields a picrate, m.p. 225.5-226°C and a picrolonate, m.p. 109- 110°C. The ultraviolet spectrum shows a single absorption maximum at 219 mp.. Several crystalline salts and derivatives are known, e.g. the aurichloride, m.p. 182.5-183.5°C; platinichloride, m.p. 196-7°C (dec.); bitartrate, m.p. 201°C; reineckate, m.p. 169-171°C; picrate, m.p. 225- 225.5°C; picrolonate, m.p. 138°C and the methiodide, m.p. 194-6°C (dec.). The O-acetate occurs naturally (q.v.) in Senecio kirkii.

Uses

Senkirkin, a pyrrolizidine alkaloid, occured in the aerial parts of the medicinal plant Tussilago farfara, could induce chromosome damage in human lymphocytes. Senkirkin can be metabolized by CYP3A4[1].

Definition

ChEBI: Senkirkine is a macrolide.

Safety Profile

Poison by ingestion and intraperitoneal routes. Questionable carcinogen with experimental neoplastigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of Nox

References

Briggs, Mangan, Russell., J. Chern. Soc., 1891 (1948)
Massagetov, Kuzovkov.,J. Gen. Chern., USSR, 23, 158 (1953)
Danilova, Konovalova., ibid, 30, 1921 (1961)
Danilova, Koretskaya, Utkin., ibid, 31, 3815 (1961)
Wunderlich., Chern. Ind., 2089 (1962)
Briggs et al., J. Chern. Soc., 2492 (1965)

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